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The antinociceptive evaluation of 2,3-substituted-1,3-thiazolidin-4-ones through thermal stimulation in mice

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Abstract

The present study assessed the 2,3-substituted-1,3-thiazolidin-4-ones antinociceptive potential looking at the acute nociception model induced by thermal stimulation in mice. This was done to contribute to the development of new analgesic drugs, in addition to the fact that 4-thiazolidinones are an important scaffold associated with many pharmacological activities. The synthesized compounds were characterized by GC-MS and NMR of 1H and 13C and administered at a dose of 100 mg/kg hydrochloride salt (ip). Sodium dipyrone (250 and 500 mg/Kg; ip) and tramadol hydrochloride (25 and 50 mg/Kg; ip) were used as positive controls. The hot plate test was done at a temperature of 50 ± 0.1 °C and animals assessed at 30, 60, and 90 min after the drugs were administered. Among the fourteen compounds tested, nine (5Aa, 5Ab, 5Ac, 5Ad, 5Ba, 5Bb, 5Bd, 5Ea, and 5Fa) showed significant increases in latency time when compared to saline (negative control) and compared to sodium dipyrone (500 mg/Kg; ip) in a 30-min assessment. The highest latency times were obtained for 3-(2-piperidin-1-yl)ethyl)thiazolidin-4-one derivatives (5Ab, 5Ac, and 5Ad). This highlights three findings about the chemical structure that improve activity: (i) an ethylenic link; (ii) a six-membered piperidine; (iii) an aliphatic substituent at the 2-position of thiazolidinone ring.

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Acknowledgements

The authors thank UFPel and FAPERGS (proc. 11/2068-7) for financial support. Fellowships granted to A.H.S.N. by CAPES, D.S.S by CAPES/FAPERGS and W.C. by CNPq (proc. 308791/2015-0).

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Authors and Affiliations

  1. Programa de Pós-Graduação em Bioquímica e Bioprospecção, Centro de Ciências Químicas Farmacêuticas e de Alimentos, Universidade Federal de Campus Universitário s/n° cx postal 354, Pelotas, RS, 96010-900, Brazil

    Arthur H. S. Neves, Daniel S. da Silva, Geonir M. Siqueira, Giovana D. Gamaro, Wilson Cunico & Adriana L. da Silva

  2. Departamento de Fisiologia e Farmacologia, Instituto de Biologia, Universidade Federal de Pelotas, Campus Universitário s/n° cx postal 354, Pelotas, RS, 96010-900, Brazil

    Arthur H. S. Neves & Adriana L. da Silva

  3. Laboratório de Química Aplicada a Bioativos, Centro Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Campus Universitário s/n° cx postal 354, Pelotas, RS, 96010-900, Brazil

    Daniel S. da Silva, Geonir M. Siqueira & Wilson Cunico

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  1. Arthur H. S. Neves
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  2. Daniel S. da Silva
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  3. Geonir M. Siqueira
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  4. Giovana D. Gamaro
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Correspondence to Wilson Cunico or Adriana L. da Silva.

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Neves, A.H.S., da Silva, D.S., Siqueira, G.M. et al. The antinociceptive evaluation of 2,3-substituted-1,3-thiazolidin-4-ones through thermal stimulation in mice. Med Chem Res 27, 186–193 (2018). https://doi.org/10.1007/s00044-017-2052-1

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